I have a copy of a map of Arkansas, Mississippi and Louisiana, published by A. J. Johnson, New York, 1866.

It shows the road to Gaines Landing from Monticello as:

From Monticello it tends SE 3 miles to Rough and Ready
Then 12 miles ESE to Cut Off
From Cut Off 9 miles just North of East to Bowden
Then South and then East to Barthholomeu
Thence on the Gaines Landing